WO2014098424A1 - Composition adhésive - Google Patents

Composition adhésive Download PDF

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Publication number
WO2014098424A1
WO2014098424A1 PCT/KR2013/011603 KR2013011603W WO2014098424A1 WO 2014098424 A1 WO2014098424 A1 WO 2014098424A1 KR 2013011603 W KR2013011603 W KR 2013011603W WO 2014098424 A1 WO2014098424 A1 WO 2014098424A1
Authority
WO
WIPO (PCT)
Prior art keywords
adhesive composition
sensitive adhesive
formula
pressure
monomer
Prior art date
Application number
PCT/KR2013/011603
Other languages
English (en)
Korean (ko)
Inventor
최한영
허지혜
Original Assignee
동우화인켐 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 동우화인켐 주식회사 filed Critical 동우화인켐 주식회사
Publication of WO2014098424A1 publication Critical patent/WO2014098424A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition excellent in antistatic properties and durability.
  • a liquid crystal display device In general, a liquid crystal display device (LCD) is provided with a liquid crystal cell and a polarizing plate containing a liquid crystal, and an appropriate pressure-sensitive adhesive layer for bonding them is used.
  • the pressure sensitive adhesive is often used an acrylic pressure sensitive adhesive based on an acrylic copolymer having excellent adhesiveness and transparency.
  • peeling the release film from the pressure-sensitive adhesive layer generates static electricity.
  • the generated static electricity affects the alignment of the liquid crystal and causes defects or flows between the liquid crystal cell and the adhesive due to electrostatic attraction. It causes contamination by foreign objects.
  • an ionic antistatic agent is mixed and used in the pressure-sensitive adhesive composition, but a bleed out phenomenon that precipitates due to the surface migration of the ionic antistatic agent may cause lifting, bubbles, and peeling. In particular, this problem may be exacerbated when exposed to a high temperature or high temperature and high humidity environment.
  • An object of the present invention is to provide a pressure-sensitive adhesive composition excellent in durability as well as antistatic properties because there is no phenomenon such as lifting, bubbles and peeling due to the surface migration of the antistatic agent.
  • the present invention provides an adhesive composition containing an acrylic copolymer containing a polymerizable hetero monomer having a ⁇ -hetero atom and an ionic antistatic agent.
  • the polymerizable hetero monomer having the ⁇ -hetero atom may be at least one selected from monomers of the following Chemical Formulas 1 to 8.
  • R ⁇ 1> is hydrogen or a methyl group.
  • the acrylic copolymer may contain a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and a polymerizable hetero monomer having a ⁇ -hetero atom.
  • the polymerizable hetero monomer having a ⁇ -hetero atom may be contained in an amount of 5 to 20 parts by weight based on 100 parts by weight of a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.
  • the ionic antistatic agent is a cation selected from the group consisting of alkali metal salts, ammonium salts, sulfonium salts and phosphonium salts; It may be an ionic salt consisting of an anion selected from the group consisting of fluorine-containing inorganic salts, fluorine-containing organic salts and iodine ions.
  • the ionic antistatic agent may contain 0.1 to 5 parts by weight based on 100 parts by weight of the acrylic copolymer.
  • the pressure-sensitive adhesive composition may further contain a crosslinking agent.
  • the pressure-sensitive adhesive composition of the present invention is free from phenomena such as lifting, bubbles, and peeling due to the surface migration of the antistatic agent, and the cohesive force is improved, which is not only excellent in durability but also satisfactory antistatic property.
  • the pressure-sensitive adhesive composition has an advantage of high utilization in the static electricity avoidance applications in the field of plastic products, especially electrical / electronic devices, such as static electricity is easily generated.
  • the present invention relates to a pressure-sensitive adhesive composition excellent in antistatic properties and durability.
  • the pressure-sensitive adhesive composition of the present invention contains an acrylic copolymer containing a polymerizable hetero monomer having a ⁇ -hetero atom and an ionic antistatic agent.
  • the polymerizable hetero monomer having a ⁇ -hetero atom contained in the acrylic copolymer may improve compatibility by promoting the chelating action of the hetero ring structure with the cation of the antistatic agent.
  • the bleed out phenomenon in which the antistatic agent component moves to the surface and precipitates is suppressed by the improvement of the compatibility, and the durability is excellent. This phenomenon can be suppressed even under high temperature or high temperature / humidity environment, thereby maintaining excellent durability.
  • ⁇ -hetero atoms contained in the acrylic copolymer may form a ring structure to increase the glass transition temperature (Tg) and rigidity of the pressure-sensitive adhesive to improve the cohesive force of the pressure-sensitive adhesive composition, thereby exhibiting more excellent durability.
  • the polymerizable hetero monomer having the ⁇ -hetero atom may be at least one selected from monomers of the following Chemical Formulas 1 to 8.
  • R ⁇ 1> is hydrogen or a methyl group.
  • the acryl-type copolymer of this invention contains the (meth) acrylate monomer which has a C1-C12 alkyl group, and the polymerizable hetero monomer which has a (beta) -hetero atom.
  • (meth) acrylate means acrylate and methacrylate.
  • Examples of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, and 2-ethylhexyl (meth).
  • the polymerizable hetero monomer having a ⁇ -hetero atom is preferably included in an amount of 5 to 20 parts by weight, more preferably 7 to 15 parts by weight, based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms. It is good. If the content is less than 5 parts by weight, the bleed-out phenomenon of the ionic antistatic agent may not be suppressed and durability may be reduced. If the content is more than 20 parts by weight, the adhesion may be reduced due to lack of tack. Due to the polarity, physical properties such as heat and humidity can be reduced.
  • the acrylic copolymer of the present invention may further contain a polymerizable monomer having a crosslinkable functional group in addition to the polymerizable hetero monomer having the ⁇ -hetero atom.
  • the polymerizable monomer having a crosslinkable functional group has a function of imparting cohesive force or adhesive strength by chemical bonding with the following crosslinking agent, and includes a monomer having a hydroxy group, a monomer having a carboxyl group, a monomer having an amide group, and a monomer having a tertiary amine group. Etc. can be mentioned. These can be used individually or in mixture of 2 or more types.
  • Monovalent acids such as (meth) acrylic acid and a crotonic acid; Diacids such as maleic acid, itaconic acid and fumaric acid, and monoalkyl esters thereof; 3- (meth) acryloylpropionic acid; Succinic anhydride ring-opening adduct of 2-hydroxyalkyl (meth) acrylate with 2-3 carbon atoms of an alkyl group, Succinic anhydride ring opening adduct of hydroxyalkylene glycol (meth) acrylate with 2-4 carbon atoms of an alkylene group And a compound obtained by ring-opening addition of succinic anhydride to a caprolactone adduct of 2-hydroxyalkyl (meth) acrylate having 2 to 3 carbon atoms of an alkyl group, among which (meth) acrylic acid is preferred.
  • Examples of the monomer having an amide group include (meth) acrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, 3-hydroxypropyl (meth) acrylamide, 4-hydroxybutyl (meth) acrylamide, 6 -Hydroxyhexyl (meth) acrylamide, 8-hydroxyoctyl (meth) acrylamide, 2-hydroxyethylhexyl (meth) acrylamide, etc. are mentioned, Among these, (meth) acrylamide is preferable.
  • Monomers having a tertiary amine group include N, N- (dimethylamino) ethyl (meth) acrylate, N, N- (diethylamino) ethyl (meth) acrylate, and N, N- (dimethylamino) propyl (meth ) Acrylates and the like.
  • a crosslinkable monomer is contained in 0.05-10 weight part with respect to 100 weight part of total monomers used for manufacture of an acryl-type copolymer, More preferably, it is 0.1-8 weight part. If the content is less than 0.05 parts by weight, the cohesive force of the pressure-sensitive adhesive may be reduced, the durability may be lowered. If the content is more than 10 parts by weight, the adhesive strength is lowered by a high gel fraction may cause problems in durability.
  • polymerizable monomers in addition to the monomers may be further included in an amount of 10 parts by weight or less based on 100 parts by weight of the total monomer used in the preparation of the acrylic copolymer, such as to reduce the adhesion.
  • the production method of the copolymer is not particularly limited, and may be prepared using a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which are commonly used in the art, and solution polymerization is preferable.
  • a solvent, a polymerization initiator, a chain transfer agent for molecular weight control, and the like, which are usually used in the polymerization may be used.
  • the copolymer has a weight average molecular weight (polystyrene equivalent, Mw) measured by gel permeation chromatography (GPC) of 50,000 to 2 million, preferably 400,000 to 2 million.
  • Mw polystyrene equivalent
  • GPC gel permeation chromatography
  • the ionic antistatic agent is not particularly limited as long as it is an ionic salt composed of an anion and a cation and can impart ionic conductivity to the pressure-sensitive adhesive.
  • a cation selected from the group consisting of alkali metal salts, ammonium salts, sulfonium salts and phosphonium salts; It may be an ionic salt consisting of an anion selected from the group consisting of fluorine-containing inorganic salts, fluorine-containing organic salts and iodine ions.
  • Such an ionic antistatic agent may contain 0.1 to 5 parts by weight, preferably 0.5 to 3 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 parts by weight may be insufficient antistatic properties and if it exceeds 10 parts by weight it may be difficult to secure durability.
  • the pressure-sensitive adhesive composition of the present invention may further contain a crosslinking agent.
  • a crosslinking agent can improve adhesiveness and durability, and can maintain the reliability and shape of an adhesive at high temperature.
  • the crosslinking agent may be an isocyanate type, an epoxy type, a melamine type, a peroxide type, a metal chelate type, an oxazoline type, or the like, and one or two or more kinds thereof may be mixed. Of these, double double isocyanate type or epoxy type is preferred.
  • the isocyanate type is tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalenedi Diisocyanate compounds such as isocyanate; Diisocyanate obtained from 2 moles of an adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate obtained by self-condensing 3 moles of the diisocyanate compound, and 3 moles of the diisocyanate compound And polyfunctional isocyanate compounds containing three functional groups such as biuret, triphenylmethanetriisocyanate, and methylenebistriisocyanate, in which the remaining 1 mo
  • Examples of the melamine type include hexametholol melamine, hexamethoxymethyl melamine, hexabutoxymethyl melamine, and the like.
  • Such a crosslinking agent may be contained in an amount of 0.1 to 15 parts by weight, preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 part by weight, the cohesive force may be reduced due to insufficient crosslinking degree, thereby impairing the adhesive durability and the cleavage property. If the content is more than 15 parts by weight, problems may occur in reducing residual stress due to excessive crosslinking reaction.
  • the pressure-sensitive adhesive composition of the present invention may further include a silane coupling agent.
  • the kind of the silane coupling agent is not particularly limited, and for example, vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxy Propyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-metha Krilloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxysilane , N-2- (aminoethyl) -3-aminopropylmethyld
  • the silane coupling agent may be included in an amount of 0 to 10 parts by weight based on 100 parts by weight of the copolymer based on the solid content, preferably 0.005 to 5 parts by weight. If the content is more than 10 parts by weight, durability may be reduced.
  • the pressure-sensitive adhesive composition is a tackifying resin, antioxidant, leveling agent, surface lubricant, dye, pigment, antifoaming agent, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, etc. It may further contain additives such as fillers and light stabilizers.
  • Such additives can be appropriately adjusted in a range not impairing the effects of the present invention.
  • the pressure-sensitive adhesive composition of the present invention can be used as a pressure-sensitive adhesive for polarizing plates and a surface protective film for bonding to liquid crystal cells.
  • it can be used as a general commercial adhesive sheet product as well as a protective film, a reflective sheet, a structural adhesive sheet, a photographic adhesive sheet, a lane marking adhesive sheet, an optical adhesive product, an adhesive for electronic parts, and the like.
  • Nitrogen gas was refluxed and the monomer mixture consisting of the composition of Table 1 was added to a 1 L reactor equipped with a cooling device to facilitate temperature control, and then 100 parts by weight of ethyl acetate was added as a solvent. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 78 °C. After the mixture was uniformed, 0.03 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 8 hours to prepare an acrylic copolymer having a weight average molecular weight of about 750,000.
  • AIBN azobisisobutyronitrile
  • an acrylic copolymer, an ionic antistatic agent, a crosslinking agent, and a silane coupling agent were mixed, and then diluted in ethyl acetate to prepare a pressure-sensitive adhesive composition having a solid content concentration of 15%.
  • the pressure-sensitive adhesive composition prepared above was applied on a release film coated with a silicone release agent to have a thickness of 25 ⁇ m, and dried at 100 ° C. for 1 minute to form an adhesive layer.
  • a pressure-sensitive adhesive polarizing plate was prepared by laminating the pressure-sensitive adhesive layer prepared above on an iodine-based polarizing plate having a thickness of 185 ⁇ m. The prepared polarizing plate was stored for 20 days under conditions of 23 degreeC and 60% RH.
  • the prepared pressure-sensitive adhesive polarizing plate was measured 10 times each of three points of the pressure-sensitive adhesive layer using a surface resistance measuring instrument (MCP-HT450, Mitsubishi Chemical Co., Ltd.), and the average value thereof was represented.
  • Bubble or peeling is slightly visible but polarizer performance is maintained: ⁇

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polarising Elements (AREA)

Abstract

Cette invention concerne une composition adhésive, et plus spécifiquement, une composition adhésive comprenant : un copolymère acrylique contenant un hétéromonomère polymérisable ayant un β-hétéroatome ; et un agent antistatique ionique, ayant ainsi une longévité et des propriétés antistatiques supérieures qui permettent d'éviter le détachement, les bulles, et la séparation due à la transition de surface de l'agent antistatique et d'améliorer la force cohésive.
PCT/KR2013/011603 2012-12-20 2013-12-13 Composition adhésive WO2014098424A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2012-0149248 2012-12-20
KR1020120149248A KR20140079979A (ko) 2012-12-20 2012-12-20 점착제 조성물

Publications (1)

Publication Number Publication Date
WO2014098424A1 true WO2014098424A1 (fr) 2014-06-26

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WO (1) WO2014098424A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08304959A (ja) * 1995-04-28 1996-11-22 Mitsubishi Paper Mills Ltd 帯電防止剤およびそれを用いた感光材料
KR970042535A (ko) * 1995-12-27 1997-07-24 김용구 히드록시 헤테로 고리 알킬 아크릴 유도체 및 이의 제조방법
JP2009019176A (ja) * 2007-07-13 2009-01-29 Toyo Ink Mfg Co Ltd 帯電防止粘着剤組成物およびそれを用いてなる粘着シート
KR20090011403A (ko) * 2007-07-26 2009-02-02 동우 화인켐 주식회사 점착제 조성물 및 이를 포함한 편광판
JP2010215868A (ja) * 2009-03-19 2010-09-30 Sanyo Chem Ind Ltd 光学用粘着剤
JP2012017399A (ja) * 2010-07-07 2012-01-26 Nagase Chemtex Corp 帯電防止性粘着剤組成物、粘着剤層、粘着シート、表面保護フィルム及び偏光板
KR20120036829A (ko) * 2009-06-09 2012-04-18 닛폰고세이가가쿠고교 가부시키가이샤 점착제 조성물 및 점착제 및 광학 부재용 점착제, 이를 이용하여 얻어지는 점착제층 부착 광학 부재

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08304959A (ja) * 1995-04-28 1996-11-22 Mitsubishi Paper Mills Ltd 帯電防止剤およびそれを用いた感光材料
KR970042535A (ko) * 1995-12-27 1997-07-24 김용구 히드록시 헤테로 고리 알킬 아크릴 유도체 및 이의 제조방법
JP2009019176A (ja) * 2007-07-13 2009-01-29 Toyo Ink Mfg Co Ltd 帯電防止粘着剤組成物およびそれを用いてなる粘着シート
KR20090011403A (ko) * 2007-07-26 2009-02-02 동우 화인켐 주식회사 점착제 조성물 및 이를 포함한 편광판
JP2010215868A (ja) * 2009-03-19 2010-09-30 Sanyo Chem Ind Ltd 光学用粘着剤
KR20120036829A (ko) * 2009-06-09 2012-04-18 닛폰고세이가가쿠고교 가부시키가이샤 점착제 조성물 및 점착제 및 광학 부재용 점착제, 이를 이용하여 얻어지는 점착제층 부착 광학 부재
JP2012017399A (ja) * 2010-07-07 2012-01-26 Nagase Chemtex Corp 帯電防止性粘着剤組成物、粘着剤層、粘着シート、表面保護フィルム及び偏光板

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